Silicone quats (silicones containing quaternary ammonium groups optionally containing polyorganosiloxane substituents) are known to be highly substantive, that is, they have a high ability to bind to carriers such as, for example, fibers, keratin substances, such as hairs etc. U.S. Pat. No. 4,891,166 describes the reaction of α,ω-diepoxides with tertiary amines in the presence of acids yielding α,ω-diquaternary siloxanes. They can be used for hair care purposes. U.S. Pat. No. 4,891,166 describes tetra alkyl derivatives as well as aromatic imidazolinium derivatives.
The reaction of α,ω-diepoxides with di-tertiary amines in the presence of acids yields polyloop polyquaternary polyorganosiloxanes (U.S. Pat. No. 4,833,225). The advantage of these materials is an improved wash off resistance from hair.
The reaction of α,ω-diepoxides with dimethylamine in the presence of acids yields polyloop polyquaternary polyorganosiloxanes having one quat group between the siloxane blocks is disclosed in U.S. Pat. No. 6,730,766.
Polyquaternary imidazolinium derivates are described in U.S. Pat. No. 6,240,929. These cationic compounds possess an improved compatibility with anionic surfactants in cosmetic formulations.
The incorporation of alkylene oxide moieties in silicone quats is to further increase the hydrophilicity.
Silicone quats containing quat groups as well as polyethylene oxide moieties in side chains are described in U.S. Pat. No. 5,098,979, U.S. Pat. No. 5,153,294 and U.S. Pat. No. 5,166,297. The substantivity of the materials, i.e. their ability to bind to carriers, is relatively low.
Silicone based block copolymers containing quat functions that also include polyether moieties are described in U.S. Pat. No. 7,217,777, U.S. Pat. No. 7,041,767 and US 2002/0103094 A. The alkylene oxide structures are incorporated into the block copolymer as α,ω-difunctional moieties.
U.S. Pat. No. 6,242,554 describes α,ω-difunctional siloxane derivatives containing one polyether and one quat function separated from each other. The substantivity of these monoquats is insufficient.
U.S. Pat. No. 4,921,895 describes blends of polyethersiloxanes and quaternary ammonium groups containing siloxane block copolymers for textile finishing purposes. Here, the usage of the polyethersiloxane improves the finished goods and hydrophilicity.
US 2007/0286837, US 2007/0041929, US 2008/0292575 and CN 101198311 describe combinations between silicone quats having a siloxane chain length of greater than 200 D-units and is a second silicone for hair conditioning purposes. One possible choice of the second silicone is the choice of silicone polyethers derived from ethylene oxide or propylene oxide or mixtures thereof. Specific structures are not given.
Low viscosity polyorganosiloxanes comprising quaternary ammonium groups are described in WO 2013/148629. The incorporation of alkylene oxide moieties into low viscosity polyorganosiloxanes comprising quaternary ammonium groups is described in WO 2013/148935 and WO 2013/148635.
The advantage of these low viscosity polymers is the improved dispersibility in liquids, i.e. water. US 2013/0259820, US 2015/0093421, US 2015/0093420 describe the usage of low viscosity polyorngnosiloxanes comprising quaternary ammonium groups and alkylene oxide groups in conditioners.
US 2015/0010487 and US 2015/0011449 describe the usage of low viscosity polyorganosiloxanes comprising quaternary ammonium groups and alkylene oxide groups in shampoos.
US 2006/0223939 and US 2006/0235181 describe polyorganosiloxanes comprising quaternary ammonium groups and different hydrophilic moieties. A moiety of the structure —CH2CH(OH)CH2OCH2CH(OH)CH2OCH2CH(OH)CH2— is disclosed. Instructions for the incorporation of this desirable moiety, which is based on renewable raw materials and readily biodegradable, into low viscosity polyorganosiloxanes comprising quaternary ammonium groups are not give.
U.S. Pat. No. 6,403,061 describes UV photo-protecting W/O emulsions. Certain poly(oxyalkylated) silicones are used as W/O emulsifiers to stabilize the formulations. Disadvantage is that these poly(oxyalkylated) silicones itself and/or low molecular weight poly(oxyalkylated) monomer traces and/or by-products are suspected to have potentially a skin sensitizing effect in cosmetic applications. Furthermore hydrophilicity of such poly(oxyalkylated) silicones in some instances is not high enough to provide superior dispersibility in water.
None of the above prior art disclosures describes a straight forward methodology for the preparation of low viscosity polyorganosiloxanes comprising quaternary ammonium groups and additional functional organic groups, comprising one or more hydroxyl groups and at least one functional group selected from an ester group, an ether group and an amino group. Low viscosity materials comprising additional strongly hydrophilic hydroxylated moieties would further improve the dispersibility in water, thus reducing the system requirements during the formulation process.